- Reading Volume One becomes Harsher in Hindsight as the story progresses in the next volumes thanks to Cerebus Syndrome kicking in. Watching Mike and Lucy playing together or engaging in slapstick humor, watching Paulo and Abbey getting into arguments after meeting in high school, watching Daisy and Paulo's initial pursuit for Mike and Lucy's hearts... It's not so funny anymore when we see what happens in the following volumes.
- Anytime Lucy loses Mike, she has a heartrending emotional breakdown. It really shows just how attached she's become to him over the years. However, the single saddest moment happens in Chapter 51 "A Distance Apart" when Lucy finally admits her love for him, and he rejects her.
- There have been other tearjerkers besides the one above. How about some of Daisy's Corrupt the Cutie moments during the Awakening arc? In Rising Temperature, being humiliated by Katie and two in this page? Mike feels guilty for ignoring Daisy and Daisy is all alone, even though she does have her friends.
- Mike and Abbey's fight regarding the former neglecting Daisy in favor of spending time with Lucy. Abbey loves Daisy, but he's painfully aware that she loves Mike and is angry that Mike can't take the time to at least try to be a more attentive friend with her, to the point of him nearly getting into a fist fight with Mike despite his tendency to only use violence to be a Bully Hunter. Likewise, Mike foreshadows his frustration with his friendship with Lucy and eventual hatred for her, gets enraged at Abbey's accusations, and fights back. Considering how the two of them are the nicest members of the cast, it's jarring to see the, fight like this, particularly when Molly comes and begs them to stop fighting.
- The "Another Path" chapter is pretty much tear jerking. It's a what-if scenario of what would have happened if Paulo had a Moment of Weakness to give Lucy Sex for Solace over her heartbreak. It's quite heartbreaking to see Lucy tear up over Paulo taking her virginity and panicking over the possibility of being pregnant. Likewise, Paulo actually breaks down in tears when he tells his dad (even if it's Played for Laughs) and later as he takes care of Lucy during the time it takes to get the results of her pregnancy test, he bitterly cries in jealously over Mike being Lucy's support, admitting his anger at him for not wanting to be there for her while he wants to be there for her. By the end of the chapter, Paulo and Lucy are an Official Couple and graduating, with Lucy declaring her love for him...only for the chapter to be revealed to be All Just a Dream.
- Pillow Talk has some more tearjerkers for you. Though, YMMV on them.
- In the "December" arc, Mike finally tears into Lucy over everything she's done to him, culminating in him declaring his undying hatred for her. The worst part, he then reveals he never saw her as a friend.
- He then proceeds to take it WAY too far, especially considering that Lucy's behavior has improved, and his unnecessarily cruel words to her leave the reader with a strong desire to punch him in the face. Even a constant victim of abuse for so long like himself isn't supposed to break her to the point where she's physically ill. Poor Lucy...
- "At Loose Ends" show more of Abbey's Dark and Troubled Past, specifically, his final straw with his father, how he became a woman-protector, and his mother's death. All in the middle of the fucking Christmas season.
- "Just Beautiful" is relatively lighthearted...until Lily chases off Mike, who decided to try apologizing to Lucy for his recent behavior. Not really that sad, since he was only doing so on Sandy's advice, but then She and Lucy have to tell Yashy the truth behind Mike's status. Jesus!
- "Small Fry", despite being more of a light-hearted romp through Paulo's 16th birthday, and his foray into getting a part-time job and learning how to drive, shows us the inevitability of Rachel and Paulo's 'friends-with-benefits' relationship, especially with Paulo feeling guilty about Rachel's genuine attraction to him while he's still hoping that Lucy will one day return...
- "Total Recall", wherein at the end of the Junior Prom, where Paulo, Matt, and Jordan do some definite male bonding, they get caught right into a car accident.
- "Trapped," where Augustus has his origins with Alejandro told, and we run into a girl named Melanie... who is in an abusive relationship with Alejandro. On page 25, she reveals that the scholarship she wants is specifically to get away from Alejandro, and her breakdown over it is painful to watch.
- "Class of 2008", in which Tess graduates. After all she's been through with Paulo, as well as Jess and Rachel, it's heartrending to see her (mostly) forgiven and sent on her way with good luck wishes. The last we see of her is a hazy gray pencil sketch as she walks out of Roseville High. Especially poignant for those graduating at the time of this chapter's release.
- The splintering of the main group of friends. Before the Acapulco arc, the main clique used to be a rather tight-knit group of friends (especially the main protagonists Lucy and Mike), and despite all of the vitriol that they give each other, always had each others' backs, even willing to risk their lives to save each other when in dangerous perils. Come Sophomore year, the circle of friends slowly corrodes as internal grudges and bottled-up emotions rise and Love Triangles come forward. The absolute destruction of Mike and Lucy's friendship (with the latter being Put on a Bus) was a very critical hit to the group's stability, and even when Lucy came back in Chapter 95, the situation did not get any better. Makes it even more tragic when you realize that every single member of the group is guilty of doing something that unwittingly shatters not only their individual friendships with one another, but their entire True Companions group as a whole.
- Chapter 95 has us see Lucy's suicide attempt in gruesome, heartrending fashion. She decides to jump off a building after we're treated to a few pages of her self-loathing internal monologue. And we see her jump too... and watch her not only survive the attempt, but also realize she survived, is bleeding out, and can barely move. It's a good thing Augustus came when he did...
- Chapter 96 doesn't stop the pain train for anyone. While it's more reasonably light-hearted, the end of it has Mike get exactly what's coming to him from Lucy. With Mike pussyfooting around so much, it should have been a glorious moment, but the end and the intermission, where all the guilt culminates in him and he breaks down in tears, feels otherwise.
- Even in the light-hearted moments there's still a bit of sadness. As Mike's facing the last opponent in dodgeball, he can't quite shake off all of the violent antics Lucy did to him.
- Paulo's chances with Lucy sink hard during Chapter 97. Even though he feels like she didn't use him, Lucy tries to beat into his head that the pair was never going to happen, and their one moment was an act of desperation.
Paulo: I want off this shitty ride.
Tear Jerker / Bittersweet Candy Bowl
Probably the only webcomic that will make you cry for good reasons.